3-(Dimethylamino)phenol → HCID 53809912, compound

HRID 1613419Notes

Reaction equation

HRID 1613419 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[S:11](Cl)(=[O:14])(=[O:13])[NH2:12].C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[CH3:1][N:2]([CH3:10])[C:3]1[CH:4]=[C:5]([O:9][S:11](=[O:14])(=[O:13])[NH2:12])[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 74213-(Dimethylamino)phenolHCID 8471TriethylamineHCID 24499Chlorosulfamic acid

Product 1

HCID 53809912HCID 53809912, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
15 °C

Procedure

A solution of 3-dimethylaminophenol (6.90 g, 0.05 mole) in 30 ml of acetonitrile was added in 13 minutes to a chilled (15° C.) stirred solution of 0.10 mole sulfamoyl chloride (Preparation 19) in 30 ml of acetonitrile. This was followed by the addition of 14 ml (0.10 mole) of triethylamine. The resultant mixture was stirred at room temperature overnight. The reaction was diluted with ethyl acetate (~60 ml) and then extracted twice with sodium bicarbonate solution. The aqueous layers were back extracted with 1:1 ethyl acetate/acetonitrile once. The organic layers were combined, dried over sodium sulfate, charcoaled, filtered, and evaporated to a black oil weighing 7.57 g.

Workup

  1. extractionextracted twice with sodium bicarbonate solution
  2. extractionThe aqueous layers were back extracted with 1:1 ethyl acetate/acetonitrile once
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to a black oil

Sources & evidence

ORD record
ord-9d5e30fe474d4c90a5cd60d3b5df6687
Source dataset
uspto-grants-1993_03
Patent number
US05192785

Reaction notes

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